Ammonium Chloride → 4-Ethoxy-3-iodo-benzenamine

HRID 1593764ノート

反応式

HRID 1593764 の反応式
[Cl-].[NH4+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[I:15])[CH3:4]>C(O)C.O.[Fe]>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[I:15])[CH3:4]

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 574195081-Ethoxy-2-iodo-4-nitrobenzene

生成物 1

HCID 574195094-Ethoxy-3-iodo-benzenamine収率 96.9%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A suspension of iron (3.81 g, 70 mmol) and ammonium chloride (5.47 g, 102 mmol) in 80 mL of ethanol and 25 mL of water was heated to reflux. 1-Ethoxy-2-iodo-4-nitrobenzene (5.0 g, 20 mmol) was added in portions and the reaction was heated at reflux for 1 hour. The hot mixture was filtered through Celite, washed with hot ethanol. The filtrate was concentrated in vacuo and treated with ethyl acetate and water. The organic layer was extracted, washed with brine, dried over magnesium sulfate and filtered. Removal of the solvent in vacuo provided 5.1 g of (4-ethoxy-3-iodophenyl)amine as a light brown oil; 1H NMR (400 MHz, DMSO-d6) δ 1.30 (s, 3H), 3.89 (q, 2H), 4.82 (bs, 2H), 6.53 (dd, 1H), 6.72 (d, 1H), 7.11 (d, 1H); MS (ES) m/z263.9 (M+H)+

後処理

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 1 hour
  4. filtrationThe hot mixture was filtered through Celite
  5. washwashed with hot ethanol
  6. concentrationThe filtrate was concentrated in vacuo
  7. additiontreated with ethyl acetate and water
  8. extractionThe organic layer was extracted
  9. washwashed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customRemoval of the solvent in vacuo

出典と根拠

ORDレコード
ord-b4cd80198923468c96464ebec9a3cf44
出典データセット
uspto-grants-2007_11
特許番号
US07297795B2

反応ノート

読み込み中…